5 travel hacks on choosing the best vacation spot
As much as I travel for work, I like to carve out time for a vacation (ironically, my job is not a vacation! Unless you consider running around cities, attending three-hour meals with managers, taking notes, hotel tours, early AM wake-up calls, making time to write stories on the spot, finding story angles, constant social media, gaining weight and little time to exercise = paradise). When I do have the time to plan a vacation, I'm in the same boat as you. Where do I start??
Choosing a destination to spend your next vacation is not easy. There's stiff competition among hotels, airlines, tour operators and now vacation rentals, all of which fight hard to get your tourism dollar, and it's easier to get to places you couldn't imagine a decade ago (with better flight connectivity). In English: there's an incredible amount of great options, making it hard to decide where to go. It's like going to an ice cream parlor and stressing over what flavor to get. It can be overwhelming. You don't want any regrets (but, uhhh, go for Rocky Road).
I help dozens of friends, friends of friends, readers, extended family, colleagues and even strangers help choose a place they'll love, but I know it can be stressful planning if you don't know someone who can give solid tips. So I created a list of five questions everyone should answer to ultimately decide on the perfect vacation spot.
Five questions to ask yourself when planning your next vacation
1. What are your top ten fantasy trips at this point in time?
Your list doesn't necessarily have to include your "bucket list" (places you have to see before you die). Think of the places you want to visit now. Why? These are the places that will definitely make you instantly satisfied. Picking the top ten is quite possibly the hardest part, but think about where and why you want to go. City? Beach? Private island? Skiing? Down Under? A new luxury hotel you've been dying to check out? A food truck in a jungle everyone has raved about? When you ask yourself why you want to go, if you can't find a good enough reason, it should not be on your list right now. I highly recommend visiting a place you've never been to rather than a place you already love (you can always go back there.. why not try something new?). Also, be as specific as you can be. For instance, don't think "Hawaii" but rather "Maui."
Write down the top ten. Now cut that in half. It's tough, but this will help you identify the five places you really want to visit.
2. How much time do you have?
Unfortunately, America has a notorious low percentage of passport holders because Americans have very little vacation days. If you plan on going overseas, get your passport NOW. Based on the five places you want to visit, you should figure out what makes sense in terms of how much time you can spend there. If time is not an issue, you're golden. If it is, narrow your list even further down to destinations easiest to get to (for instance, if Hawaii and Thailand are on your list, go with Hawaii for now, as you lose two days going to Thailand). If money is not an issue, and you can group your vacation with Christmas (when hotels are at their most expensive) or Thanksgiving (when flights are expensive), you can have a longer vacation using your vacation days.
3. Is now the best time to go?
High-season destinations will be more expensive to travel to than off season (for instance, in winter, high-season would include tropical destinations like Mexico and Hawaii. Off season for winter would be cities that will be crazy cold like Copenhagen or southern Italy). You don't want to go somewhere during rainy season as you have the chance of ruining your entire trip due to weather. Also, are there cheap flights? Can you get good hotel rates? Is there a big city event that has all the hotel rooms sold out? Within your five top destinations, figure out which ones pass all these questions and are places realistically suitable to visit now.
4. Who do you want to travel with?
Trust me. It's better to decide who you want to travel with AFTER you pick the destination. Otherwise, you'll be doing a lot of compromising that could take you back to square one. If you're already planning your next big vacation with someone else in mind, then do all the questions together from the start (it might be trickier, which is why we recommend asking them after you've chosen the top five and dates.). Think about who you'd want to be with on this vacation. Lover? Family? Kids? Grandparents? The guy that works at Dunkin Donuts? Or do you want to be alone? Make sure your travel companion is someone who will appreciate where you're going. They are also great in helping narrow down the top five. Chances are they'll want to visit at least one of those places. Again, choose your travel companion after you have the top five (or agree to do it together). It's so much easier that way.
5. How much planning do you want to do?
Now that you've likely narrowed down the top five to your fantasy vacation spot, think about whether you want to do all the planning or leave it to someone else. Travel agents have made a huge comeback and, in most cases, it doesn't cost you a penny to use them. Virtuoso agents are the most qualified in terms of luxury travel, and customers get free room upgrades, breakfasts, etc, just from working with one (they get commission). Otherwise, you can hit the ground running as soon as you arrive with recommendations on restaurants and attractions from locals, concierge and friends who have visited.
Have a great trip!